Why Does Tom Waits always end up on lists like this?

If you want to get a friendly but heated argument started, just start naming singers that can’t sing. I did this by accident the other day when a friend played me the clip of then 7-year-old Connie Talbot singing “Somewhere Over the Rainbow” on “Britain’s Got Talent” (also below). There are a few points where she wobbles and eviscerates any concept of accurate pitch, but immediately follows with gut-wrenching feeling and a dynamic vibrato for her age. Overall, she “puts it across” with incredible impact, and you’d have to be pretty damn jaded (or maybe just hate kids) to not get at least a little bit of a teary eye. So the debate started when I said pretty much what I just said here, but elaborated by saying something like “but there are plenty of singers who can’t sing that we love to listen to, people like Tom Waits, or Frank Sinatra, or Fiona Apple“. That was an unfortunate choice for a short list, because if you want to get jumped by an angry mob that’s foaming at the mouth wanting to kick your ribs in with steel-toed boots, just be sure to pick at artists that have a rabid cult following that’s based more on an emotional connection to the artist than a well-considered analysis of their singing skills and gifts. Like Tom Waits. Or Barbra Streisand. Before I go on to share the expanded list that resulted from the ensuing debate, I should provide some background on how my opinions are guided. I grew up in a music store with well-tuned concert-pitch instruments around all the time, so on the one hand have an impeccable sense of pitch. On the other hand, I also love music from all over the world with all its non-western tunings and scales, and the first instrument I played with passion was the electric guitar, an instrument that can be horrifying in its lack of proper intonation. And as a singer, I have great pitch, but resort to odd styling and diction to mask my feeble or non-existent vibrato. Imagine a weird amalgam of Bing Crosby and Richard Butler of The Psychedelic Furs. So understand that this is mostly about taste, and is meant to be more about analysis and opinion than “criticism”. Feel free to chime in with your own picks, I’d like to do a followup with video clips as examples. Oh. One more thing. Bob Dylan sucks.

For the record, I actually like most of these singers, and I’m not going to specify the few I don’t.
Except Bob. I don’t know why. Bob just gets on my nerves.

First, the video of the kid that started the debate. She’s no Israel Kamakawiwo’ole, but c’mon. She was only seven at the time.

Some obvious choices for people who “can’t sing” but made a fortune doing it:

Frank Sinatra – He’s talking most of the time, usually not singing.
Johnny Cash – Often off-key, with a gravelly voiced slurred delivery.
Leonard Cohen – He’s really always just talking, but at the correct pitch.
Tom Waits – I’m not sure what he’s doing. It’s a lot like singing, but somehow it’s not singing.
Lou Reed – Another talk-singer. He should really be billed as a poet who prefers musical accompaniment.
Bob Dylan – Constantly strains with an affected nasality to hide his urban roots and sound Appalachian.
Fiona Apple – Almost constantly flat. *Really flat. But her gift wouldn’t work if she were on pitch.
Chet Baker – Immaculate pitch, and pure tone. It’s weird. He’s not “talk singing”, and in spite of a smoothly articulated vibrato, he always seems like he’s just “making sure the note stays right”. And on reflection, I guess he didn’t “make a fortune”. Too bad. He deserved it.

The young Chet Baker, if you’ve never heard him:

Two artists who “can sing” but manage to destroy songs by doing so:

Barbra Streisand and Céline Dion – Their self-aware and impressive technical proficiency ensures that every song feels like they feel, at the expense of whatever the song might have felt like.

Rock & Heavy Metal “device reliant” singers:

Guns N’ Roses’ Axl Rose and dozens of other metal singers punctuate a rather mediocre voice with tight-throated squeals or growls.
Billy Corrigan, Richard Butler – The “I have found my vocal texture and I’m sticking to it” approach.
Janis Joplin, Rod Stewart,Louis Armstrong – The “I don’t know why, but everyone loves my seemingly shredded vocal chords” phenomena.

Peter Lynch performing “What If That Guy From Smashing Pumpkins Lost His Car Keys”.
I never realized that Billy Corrigan sounded so much like Cartman from South Park.

So like I said, I plan to do a followup; I’m sure I missed dozens of possible examples. For now, I’ll leave you with an example of someone I think is one of the most talented and under-acclaimed singers across the board, singing a song I’m not too crazy about, and still managing to make me get weepy….